


Day Three: First Time

by Invictusimpala



Series: 30 Day NSFW Challenge [3]
Category: Supernatural
Genre: 30 Day NSFW Challenge, Anal Fingering, Blow Jobs, Bottom Dean, Coming Untouched, First Time, Fluff and Smut, M/M, Multiple Orgasms, Sex Toys, Top Sam
Language: English
Status: Completed
Published: 2014-11-03
Updated: 2014-11-03
Packaged: 2018-02-24 00:09:05
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,088
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2560805
Author URL: https://archiveofourown.org/users/Invictusimpala/pseuds/Invictusimpala
Summary: <blockquote class="userstuff">
              <p>Dean realizes he’s being ridiculous. This is <em>Sam</em>. This isn't anything new, the kissing part of it anyways. He leans in and presses a chaste kiss to Sam’s lips that grows more heated the longer it draws on.</p>
            </blockquote>





	Day Three: First Time

**Author's Note:**

> Thank you so much for reading, enjoy :)

It’s been awkward all day. They've been planning this for months, yes, but it doesn't help to alleviate the tension of getting on to the actual act.

There’s a bag full of everything they’ll need, everything they've decided to use, but neither of them have been back to the motel long enough to call the other, look through it for more than five minutes at a time. 

Dean gets back to the motel, and decides it’s him who’s going to call Sam, telling him to come back and get it over with.

It’s not like that, he doesn't want to just _get it over with_ , but he needs Sam here to calm his nerves about it.

While he waits for Sam to get home, he thumbs through the bottles of lube. 

There’s stuff that warms up, and lube that cools, but he doesn't want any of those, or those flavored ones. He pulls out a normal looking bottle of lube that’s unscented and unflavored, deciding that’s the best one to use. For their first time at least.

Sam arrives an hour later, looking stressed out and nervous as hell. He picks at the dirt under his fingernails, avoiding eye contact until Dean clears his throat.

They look at each other for a few seconds before ducking their heads.

“Sam, if you don’t want to do this, we don’t have to. We've only been together for a year and if you’re not ready --”

“I’m ready, Dean. Just . . . make the first move and the rest will follow, I think.” He says, and Dean nods.

“Is this good?” He holds up the bottle of lube, and Sam flushes, shrugging.

“It doesn't matter to me.”

Dean walks forward, closer to Sam, and he cups Sam’s face. They've been waiting until he’s eighteen to do the whole 'penetrative sex' thing so at least part of it will be legal.

Sam looks up at him. He’s not quite as tall as Dean, almost, and Dean is glad Sam is going to be taller than him -- strong and proud.

Dean realizes he’s being ridiculous. This is _Sam_. This isn't anything new, the kissing part of it anyways. He leans in and presses a chaste kiss to Sam’s lips that grows more heated the longer it draws on.

They breathe through their noses and between kisses so they don’t have to break away for more than a few seconds at a time.

Sam paws at Dean’s shirts until he peels them off. Sam fumbles to get his over his head and ends up getting stuck. Dean laughs, helping him out of them, and then Sam is pouncing, pinning Dean to the bed, their bodies bouncing on the mattress. 

Dean groans low in his throat as Sam kisses down it, nipping at the skin. The lube bottle is gone, but it doesn't matter right now. Finding his way back to Sam’s mouth is his priority.

Sam licks into his, biting at his bottom lip.

His cock jerks against the seam of his jeans where he’s tucked in, and he whines. It doesn't feel good, having it confined to such a small space when his cock is thickening, filling with blood because Sam is biting and sucking on his pulse point when he _knows_ he should only do that when they’re both naked. It sends Dean soaring over the edge too soon. Dean shoves at Sam’s shoulders, fumbling to get his pants undone, but Sam bats his hands out of the way.

“Sam, Sam, please.” Sam takes the button of his jeans into his mouth, popping it out with a flick of his tongue, and Dean has to close his eyes or this is going to end too soon.

Sam’s breath ghosts over his cock, and he bucks his hips up, his dick hard and tenting his boxers. Sam mouths over the head of his cock, and Dean whines as the skin underneath becomes visible through the wet fabric as Sam’s spit soaks through it. 

They've done this before, hand jobs and quick blow jobs between hunts, but never anything more. Dean’s both filled with excitement and dread at how this is going to feel. He’s never done it before, Sam is his first and he’s so happy he is.

Sam pulls his underwear down slowly, painstakingly slow, and Dean pants heavily as Sam licks up the shaft of his cock as it’s revealed. Pre-come drips down into Sam’s mouth, the skin of his heavy dick flushed an almost purple color.

“Sam, please, please, _please_ ,” he begs, and Sam hums, sucking him down to the base in one go that makes him thrust up with a harsh breath. Sam chokes for a moment before he finds a rhythm that has Dean’s toes curling into the sheets, head thrown back and eyes rolled into his head as pleasure seems to course through every vein in his body.

“Stop, stop, I’m gonna come.” Sam pulls off with a wet popping sound and Dean takes a few moments to get himself under control. Sam has always been good with his mouth.

“Are you ready, big brother?” Sam asks, lapping over his taut nipples, nibbling at his collar bones like the salty, sweaty skin he finds there is a candy he can’t get enough of.

Dean nods his head slowly.

Sam gets up from the bed, stripping himself down to nothing, and then he finds the nondescript bottle of lube with which he coats his hands in.

It’s shiny, slippery, and it feels weird when Sam finally gets a finger down there. Dean spreads his legs wider so Sam has easier access. He knows that on his stomach would be better for their first time, but he wants to be able to see Sam come rather than just feel it.

The first finger worms its way inside of him, and his brow furrows. It doesn't feels like anything, a blunt pressure barely there. 

“Can I move?” Dean nods his head. Sam spreads the lube around until he can fit a second one in. That almost hurts, feels like he’s got something going on that shouldn't be. He focuses on relaxing his muscles as much as he can. Sam pulls his fingers out to coat them in more lube before three fingers are probing around inside of him.

He almost shoots off the bed when Sam finds his prostate. His cock weeps against his stomach, hard and waiting for attention that’s not going to come for a while.

He whimpers.

“You okay, Dean?”

“Yeah, Sammy, keep going.”

Dean has no idea how Sam is going to get his cock inside of him, he’s much bigger than three fingers despite being eighteen, and Dean feels a vague sense of worry that’s overwritten by sparks of ecstasy shooting through him as he comes so hard he almost blacks out. Sam keeps rubbing over his prostate until there’s nothing left in him.

He’s left breathless, sunken into the memory foam of the bed as he whines out Sam’s name over and over. 

“Dean, talk to me. Can I keep going?” 

“ _Don’t stop_.” He growls, and Sam nods his head. He pulls out his fingers and positions his hips over Dean’s.

He’s still coming down, floating somewhere else, but he’s pulled back down when Sam’s cock-head is pressed up against his hole, pushing inside inch by inch at a time.

Dean’s jaw drops, rough breaths coming faster and faster. 

It feels like he’s being split open, ripped apart and put back together over and over.

His cock is soft, but Sam is hard, unrelenting until he bottoms out with a grunt.

“Dean, Dean, _oh my god_.” 

Dean breathes in through his nose and out through his mouth as Sam pets his hair, his sides, touches any part of him that he can.

“Move, _god dammit_ , _move_ ,” he groans, and Sam moves his hips a little, causing Dean to cry out silently, for Sam to drop his arms around Dean’s head.

They get situated before moving again. Sam is hugging Dean close, his arms around Dean’s head, Dean’s head buried in his neck as is Sam’s in Dean’s. Dean wraps his arms around Sam’s waist, pulling him into each thrust, and it feels weird at first, but after Sam hits his prostate for the first time, it’s heaven.

Dean moans loudly, calling out whenever Sam hits his sweet spot, and he’s hard again in no time, panting and whining, begging Sam to move faster, _please _.__

__“Sam, _harder_.” Sam’s thrusts are short, but deep, and it makes Dean’s toes bite into Sam’s skin, his fingers digging into Sam’s sides._ _

__Sam’s breath is hot in his ear as he whispers dirty things, about how well Dean’s taking his cock, about how tight Dean is. He tells Dean how good he is, so perfect for his little brother._ _

__Dean’s back arches up, his chest pressed flush with Sam’s as he comes between their bellies, untouched. It feels like it’s ripped from him unexpectedly, torn out of his clutches by Sam who’s coming inside of him, screaming into Dean’s skin._ _

__Dean pulls Sam’s head up by his hair, slamming their lips together and he tastes blood, but it doesn't matter._ _

__Dean moans are broken, choked off as Sam keeps pounding into him. His eyes cross, eyelids fluttering shut. All he can do is hold on for the ride and hope he doesn't fly apart because he feels like he’s about to._ _

__Just when it’s becoming too much, Sam pulls out slowly, slumping beside him. Dean feels stripped completely, like Sam has finally seen all of him and he’s seen the deepest part of Sam in return._ _

__Sam gets up for a wash cloth. There’s come dripping down the insides of Dean’s thighs, and it would be gross if it weren't Sam’s._ _

__The washcloth is cold, and he’d squirm away if he weren't absolutely, one hundred percent spent. He feels heavy, his limbs won’t cooperate, and he’s done trying to move them._ _

__Sam wipes between his legs until he’s clean, and then he’s back on top of Dean, keeping him warm. He grabs Dean, tugging him into his side, and Dean hums contentedly. He misses the feeling of being filled, close to Sam, so close, he needs Sam to be nearer, pressed against him like that again. It feels like Sam is miles away, or maybe he's miles away, he thinks, as he wraps his arms around Sam._ _

__“Sammy, Sammy.”_ _

__“M’right here, Dean. Did so well, big brother, you’re so good for me.” Sam plants a kiss on his sweaty forehead._ _

__“Lo’ you.”_ _

__“I love you, too. Go to sleep, I won’t leave in the morning, okay? Not even for breakfast until I know you’re okay.”_ _

__“M’fine.”_ _

__“Sure, Dean. You look like you've just been beaten to death.”_ _

__“Gee, thanks.” Dean slurs._ _

__Sam laughs, pulling Dean impossibly closer._ _

__“Are you feeling okay, though? Honestly, Dean, tell me. You can tell me it sucked, it won’t hurt my feelings.” Dean rolls his eyes._ _

__“Sam, I think that’s the best I've felt in my entire life, and we’re doing that again as soon as I wake up, so get to sleep so time’ll go faster.”_ _

__Sam kisses him on the lips. It’s a slow passing of tongues, slide of lips, and Dean lets himself fall into it._ _

__The next morning, Sam is in the shower when he wakes. His ass hurts like hell, all of his muscles protesting like they do after a three hour workout. His cock is hard under the sheets, thoughts of last night making his libido shoot through the roof. He lifts the sheets and finds finger-shaped bruises all over his hips that make him groan._ _

__Sam comes out, gives Dean one glance, grinning at his cock that’s obvious through the thin sheets._ _

__“Already, Dean, really?”_ _

__Dean stretches, a loud moan escaping his throat, and Sam shoots him a dark look._ _

__“Are we going to use those toys in the box, or am I going to have to send them back?” Sam tears the lid off and digs through the toys._ _

__Dean comes three times throughout the day from the vibrator Sam uses. He feels alive, in love, and happier than he ever has been, Sam curled into his side. Everything is still hazy from those orgasms, and it’s probably because of that that he’s imagining Sam beside him for the rest of their future together, but he won’t remember in the morning, so it doesn't matter that he’s being cheesy._ _

____

**Author's Note:**

> [My Tumblr](http://www.invictus-impala.tumblr.com)  
>  I am taking prompts there, if you're interested :)  
> (More info on that [here](http://invictus-impala.tumblr.com/post/99871679299/about-prompts-im-now-taking-prompts-yay-if-you))


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